CH217493A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH217493A CH217493A CH217493DA CH217493A CH 217493 A CH217493 A CH 217493A CH 217493D A CH217493D A CH 217493DA CH 217493 A CH217493 A CH 217493A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminoanthraquinone
- anthraquinone
- mixture
- carboxylic acid
- acid
- Prior art date
Links
- 239000000984 vat dye Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- ASDLSKCKYGVMAI-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ASDLSKCKYGVMAI-UHFFFAOYSA-N 0.000 claims description 4
- 239000007859 condensation product Substances 0.000 claims description 4
- 150000002828 nitro derivatives Chemical class 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 2
- KSDKUTSQPZBFLM-UHFFFAOYSA-N 5-nitro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound [N+](=O)([O-])C1=CC=CC=2C(C3=CC(=CC=C3C(C12)=O)C(=O)O)=O KSDKUTSQPZBFLM-UHFFFAOYSA-N 0.000 claims description 2
- ULDGECWNAPEFTD-UHFFFAOYSA-N 8-nitro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ULDGECWNAPEFTD-UHFFFAOYSA-N 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- DDDGGJDPYJAFSW-UHFFFAOYSA-N nitroformyl chloride Chemical class [O-][N+](=O)C(Cl)=O DDDGGJDPYJAFSW-UHFFFAOYSA-N 0.000 claims description 2
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 210000002268 wool Anatomy 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- DAZLBCIMRZNCRV-UHFFFAOYSA-N aniline;sodium Chemical compound [Na].NC1=CC=CC=C1 DAZLBCIMRZNCRV-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
- C09B5/40—Condensation products of benzanthronyl-amino-anthraquinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass man neue, wertvolle Küpenfarbsto@ffe erhält, wenn man Verbindungen der allgemeinen Formel
EMI0001.0006
in der R Wasserstoff oder .den Rest .eines verküpbaren Amines der Anthrachinonreihe bedeutet, mit alkalischen Kondensations- mitteln unter solchen Reaktionsbedingungen behandelt,
dass eine Verseifung der Carbon. ami:dgruppe vermieden wird. Man erreicht dies beispielsweise durch Erhitzen des Aus- ga.ngsma.terials mit Ätzalkalien in indifferen ten Lösungsmitteln, wie z. B. Pyridin oder Aininoäthanol. Man erhält dabei unter Ringschluss Verbindungen, denen voraus sichtlich die folgende allgemeine Formel zukommt:
EMI0002.0008
in der R die gleiche Bedeutung hat, wie vor , stehend angegeben.
Die neuen Farbstoffe liefern auf Baum volle wertvolle olive bis braune Farbtöne von guten Echtheitseigenschaften. Durch Nachbehandlung der Farbstoffe mit halo- genierenden Mitteln wird in vielen Fällen, ein klarerer Farbton, sowie eine bessere Chlorechtheit, der mit diesen nachhalogenier- ten Farbstoffen erhältlichen Färbungen erzielt.
Vorliegendes Patent bezieht sich nun auf ein Verfahren zur Herstellung eines Küpen- farbstoffes, dadurch gekennzeichnet, dass man ein Gemisch von 1-Aminoarithraehinon- 6-earboyl-1'-aminoanthrachinon und von 1 - Aminoanthrachinon - 7 - carboyl -1'- amino- anthrachinon, erhältlich durch Nitrieren der Anthrachinon-2-carbonsäure in Gegenwart von Schwefelsäuremonohydrat und Borsäure beti Temperaturen unter 10 C,
wodurch ein Gemisch von 1-Nitroanthrachinon-6-carbon- säure und 1-Nitro-antlirachinon-7-carbon- säure erhalten wird, Überführung dieses Ge misches in die entsprechenden Nitrocarbon- säurechloride, Kondensation der letzteren mit 1- Aminoanthrachinon und Reduktion der erhaltenen Nitroverbindungen zu den entsprechenden Aminoverbindungen, mit Bz,
-Bronibenzanthron kondensiert und das erhaltene Kondensationsprodukt mit einem Alkadihydroxyd in Gegenwart eines indiffe renten Lösungsmittels erhitzt.
Der so erhaltene Küpenfarbstoff löst sich in konzentrierter Schwefelsäure mit grüner Farbe und färbt Baumwolle aus blauschwar zer Küpe in sehr echten gelbstichig oliv grünen Tönen.
Beispiel: 47 Teile 1-Aminoanthrachinon-6- bezw. -7-carboyl-1'-aminoanthrachinon (hergestellt durch Umküpen der entsprechenden Nitro- verbindung) werden mit dl Teilen Bzl-Brom- benzanthron unter Zusatz von 25 Teilen Na triumacetat und 2 Teilen Kupferehlorür durch etwa 12stündiges Kochen in Nitro- benzol kondensiert. Das Kondensationspro dukt,
das sich in konzentrierter Schwefel säure mit gelbbrauner Farbe löst und aus braunvioletter Küpe auf Baumwolle in nur mässig echten braunen Tönen aufzieht, wird auf die übliche Weise abgetrennt und ge trocknet.
50 Teile dieses Kondensationsproduktes werden in fein verteilter Form mit einer Lösung von 50 Teilen Ätzkali in 250 Teilen Aininoäthanol während zwei Stunden auf 100 bis 110 C erhitzt.
Durch Verdünnen der Schmelze mit Wasser und Ausblasen mit Luft, gegebenenfalls auch durch Ansäuern, wird der gebildete neue Farbstoff aus- ge2chieden. Dem Farbstoff kommt wahr scheinlich folgende Formel zu:
EMI0003.0005
beziehungsweise
EMI0003.0006
Die gleiche Verbindung erhält man, wenn man als Kondensationsmittel Ätzkali unter Zusatz von Pyiidin oder auch Anilinnatrium verwendet.
Process for the production of a vat dye. It has been found that new, valuable vat dyes are obtained when using compounds of the general formula
EMI0001.0006
in which R denotes hydrogen or the remainder of a viable amine of the anthraquinone series, treated with alkaline condensing agents under such reaction conditions,
that a saponification of the carbon. ami: dgruppe is avoided. This can be achieved, for example, by heating the starting material with caustic alkalis in indifferent solvents, such as B. pyridine or aminoethanol. Compounds are obtained with ring closure which are expected to have the following general formula:
EMI0002.0008
in which R has the same meaning as stated above.
The new dyes provide valuable olive to brown color shades with good fastness properties on trees. Post-treatment of the dyes with halogenating agents in many cases results in a clearer shade and better chlorine fastness in the dyeings obtainable with these post-halogenated dyes.
The present patent now relates to a process for the production of a vat dye, characterized in that a mixture of 1-aminoarithraehinone-6-earboyl-1'-aminoanthraquinone and 1-aminoanthraquinone-7-carboyl-1'-amino- anthraquinone, obtainable by nitrating anthraquinone-2-carboxylic acid in the presence of sulfuric acid monohydrate and boric acid at temperatures below 10 C,
whereby a mixture of 1-nitroanthraquinone-6-carboxylic acid and 1-nitro-anthraquinone-7-carboxylic acid is obtained, conversion of this mixture into the corresponding nitrocarboxylic acid chlorides, condensation of the latter with 1-aminoanthraquinone and reduction of the obtained Nitro compounds to the corresponding amino compounds, with Bz,
-Bronibenzanthron condensed and the condensation product obtained is heated with an alkadihydroxide in the presence of an indifferent solvent.
The vat dye thus obtained dissolves in concentrated sulfuric acid with a green color and dyes cotton from a blue-black vat in very genuine yellowish olive-green tones.
Example: 47 parts of 1-aminoanthraquinone-6- resp. -7-carboyl-1'-aminoanthraquinone (prepared by vaporizing the corresponding nitro compound) are condensed with dl parts of Bzl-bromobenzanthrone with the addition of 25 parts of sodium acetate and 2 parts of copper chloride by boiling in nitrobenzene for about 12 hours. The condensation product
which dissolves in concentrated sulfuric acid with a yellow-brown color and grows from a brown-violet vat on cotton in only moderately genuine brown tones, is separated off and dried in the usual way.
50 parts of this condensation product are finely divided with a solution of 50 parts of caustic potash in 250 parts of aminoethanol and heated to 100 to 110 ° C. for two hours.
The new dye formed is separated out by diluting the melt with water and blowing it out with air, if necessary also by acidification. The dye is likely to have the following formula:
EMI0003.0005
respectively
EMI0003.0006
The same compound is obtained if caustic potash with the addition of pyiidine or aniline sodium is used as the condensing agent.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE217493X | 1939-06-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH217493A true CH217493A (en) | 1941-10-31 |
Family
ID=5830776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH217493D CH217493A (en) | 1939-06-06 | 1940-06-01 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH217493A (en) |
-
1940
- 1940-06-01 CH CH217493D patent/CH217493A/en unknown
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